1449519-80-5Relevant articles and documents
1,2-Hydride Migration in Dialkyl α-Diazophosphonates Catalyzed by [Cu(MeCN)4]PF6: A Novel Approach to β-Amino (E)-Enylphosphonates
Ge, Haihong,Liu, Shuang,Cai, Yan,Sun, Yuchao,Miao, Zhiwei
, p. 448 - 454 (2016/01/28)
The regiospecific and stereoselective 1,2-migration reaction of dialkyl α-diazophosphonates for the synthesis of β-amino (E)-enylphosphonates is developed utilizing tetrakis(acetonitrile)copper(I) hexafluorophosphate [Cu(MeCN)4PF6] as the catalyst and N,N-dimethylformamide as an additive. A possible mechanism for the 1,2-migration reaction involving a metal carbene is presented. An investigation on the E/Z isomer selectivity of this process demonstrates that steric factors play an important role on the outcome. This process provides a straightforward access to β-amino (E)-enylphosphonates in moderate to good yields.
Trifluoroborane-catalyzed C-H functionalization/S-H insertion reaction: Construction of N,S-acetal quaternary centers
Cai, Yan,Ge, Haihong,Sun, Weize,Miao, Zhiwei
, p. 1669 - 1677 (2015/06/02)
Abstract The trifluoroborane-catalyzed C-H functionalization/S-H insertion reaction of α-diazophosphonates with thiols has been developed. A plausible reaction mechanism has been proposed to understand the combined reaction. This process provides straightforward access to N,S-acetals containing quaternary centers in moderate to good yields and chemoselectivity.
Unexpected stereoselective synthesis of (Z)-β-alkenyl substituted β-amino phosphonates through β,γ-dihydrogen shift reaction catalyzed by a copper(I) complex and iodine [Cu(MeCN)4]PF 6/I2
Cai, Yan,Lyu, Hairong,Yu, Chengbin,Miao, Zhiwei
, p. 596 - 602 (2014/05/20)
A series of dialkyl a-diazophosphonates has been prepared from natural amino acids. The diazo decomposition of these diazophosphonate compounds with tetrakis(acetonitrile)copper(I) hexafluorophosphate/iodine, [Cu(MeCN) 4]PF6/I2, as catalyst has been investigated. It was found that the diazo decomposition of dialkyl a-diazophosphonates gave a mixture of β,γ-dihydrogen shift and 1,2-hydride migration products and afforded β-alk- enyl-substituted β-amino phosphonates with the Z configuration. The mechanism of this novel diazo decomposition process was discussed.
Combined C-H functionalization/O-H insertion reaction to form tertiary β-alkoxy substituted β-aminophosphonates catalyzed by [Cu(MeCN) 4]PF6
Cai, Yan,Lu, Yuchen,Yu, Chengbin,Lyu, Hairong,Miao, Zhiwei
, p. 5491 - 5499 (2013/09/02)
The copper-catalyzed C-H functionalization/O-H insertion reaction of α-diazophosphonates with alcohols has been developed with iodine as an additive. In order to understand this reaction, we present here a possible mechanism for the combined reaction. This process provides straightforward access to tertiary β-alkoxy substituted β-aminophosphonate derivatives with moderate to good yields. The Royal Society of Chemistry.
